GB1309324A - Uracil derivatives - Google Patents
Uracil derivativesInfo
- Publication number
- GB1309324A GB1309324A GB3908070A GB3908070A GB1309324A GB 1309324 A GB1309324 A GB 1309324A GB 3908070 A GB3908070 A GB 3908070A GB 3908070 A GB3908070 A GB 3908070A GB 1309324 A GB1309324 A GB 1309324A
- Authority
- GB
- United Kingdom
- Prior art keywords
- uracil
- reacting
- prepared
- dimethyl
- chloro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical class O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 title abstract 9
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 229940035893 uracil Drugs 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 4
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 abstract 4
- -1 CF 3 Chemical group 0.000 abstract 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- OTSKHUNLOQPIGN-UHFFFAOYSA-N 1,3,5-trimethyl-1,3-diazinane-2,4,6-trione Chemical compound CC1C(=O)N(C)C(=O)N(C)C1=O OTSKHUNLOQPIGN-UHFFFAOYSA-N 0.000 abstract 1
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 abstract 1
- VVSASNKOFCZVES-UHFFFAOYSA-N 1,3-dimethyl-1,3-diazinane-2,4,6-trione Chemical compound CN1C(=O)CC(=O)N(C)C1=O VVSASNKOFCZVES-UHFFFAOYSA-N 0.000 abstract 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 abstract 1
- HBJDKUILXQYCHV-UHFFFAOYSA-N 1-butyl-1,3-diazinane-2,4,6-trione Chemical compound CCCCN1C(=O)CC(=O)NC1=O HBJDKUILXQYCHV-UHFFFAOYSA-N 0.000 abstract 1
- ZTUIKEVPLFQEJR-UHFFFAOYSA-N 1-cyclohexyl-1,3-diazinane-2,4,6-trione Chemical compound O=C1NC(=O)CC(=O)N1C1CCCCC1 ZTUIKEVPLFQEJR-UHFFFAOYSA-N 0.000 abstract 1
- MECMQZBUZCGXQW-UHFFFAOYSA-N 1-phenyl-1,3-diazinane-2,4,6-trione Chemical compound O=C1NC(=O)CC(=O)N1C1=CC=CC=C1 MECMQZBUZCGXQW-UHFFFAOYSA-N 0.000 abstract 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 abstract 1
- VATQPUHLFQHDBD-UHFFFAOYSA-N 6-chloro-1,3-dimethylpyrimidine-2,4-dione Chemical compound CN1C(Cl)=CC(=O)N(C)C1=O VATQPUHLFQHDBD-UHFFFAOYSA-N 0.000 abstract 1
- 101710134784 Agnoprotein Proteins 0.000 abstract 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 abstract 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 229940035676 analgesics Drugs 0.000 abstract 1
- 239000000730 antalgic agent Substances 0.000 abstract 1
- 229940125715 antihistaminic agent Drugs 0.000 abstract 1
- 239000000739 antihistaminic agent Substances 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 230000036772 blood pressure Effects 0.000 abstract 1
- CNWSQCLBDWYLAN-UHFFFAOYSA-N butylurea Chemical compound CCCCNC(N)=O CNWSQCLBDWYLAN-UHFFFAOYSA-N 0.000 abstract 1
- 210000001326 carotid sinus Anatomy 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 125000005358 mercaptoalkyl group Chemical group 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 229940125723 sedative agent Drugs 0.000 abstract 1
- 239000000932 sedative agent Substances 0.000 abstract 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 abstract 1
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/553—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms with halogen atoms or nitro radicals directly attached to ring carbon atoms, e.g. fluorouracil
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/557—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. orotic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/60—Three or more oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Communication Cables (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1942405A DE1942405C3 (de) | 1969-08-20 | 1969-08-20 | Arylsubstituierte Piperazinylpropylenaminouracile |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1309324A true GB1309324A (en) | 1973-03-07 |
Family
ID=5743321
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3908070A Expired GB1309324A (en) | 1969-08-20 | 1970-08-13 | Uracil derivatives |
Country Status (24)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116082250A (zh) * | 2021-11-05 | 2023-05-09 | 江苏润安制药有限公司 | 一种新的制备盐酸乌拉地尔的方法 |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2329399A1 (de) * | 1973-06-08 | 1975-01-02 | Wuelfing J A Fa | 4-alkyl-aminouracile, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| LU74319A1 (enrdf_load_stackoverflow) * | 1976-02-09 | 1977-08-19 | ||
| DE3326118A1 (de) | 1982-08-02 | 1984-02-09 | Byk Gulden Lomberg Chemische Fabrik Gmbh, 7750 Konstanz | Pyridopyrimidintrione, verfahren zu ihrer herstellung, ihre verwendung und sie enthaltende arzneimittel |
| IE62890B1 (en) * | 1988-12-06 | 1995-03-08 | Hafslund Nycomed Pharma | New piperazinylalkyl-3(2h)-pyridazinones process for the preparation thereof and the use thereof as agents lowering blood pressure |
| CA2024428A1 (en) * | 1989-09-06 | 1991-03-07 | Masayuki Ishikawa | Agent for treating urinary obstruction |
| WO1991011185A1 (de) * | 1990-02-01 | 1991-08-08 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Verwendung von urapidil und derivaten zur behandlung arteriosklerotische erkrankungen |
| DE4425143A1 (de) * | 1994-07-15 | 1996-01-18 | Basf Ag | Substituierte Pyrimidinverbindungen und deren Verwendung |
| EP0796251B1 (de) * | 1994-12-07 | 2001-10-17 | Byk Gulden Lomberg Chemische Fabrik GmbH | Uracilderivate |
| EP1118322A4 (en) | 1998-09-30 | 2004-10-20 | Takeda Chemical Industries Ltd | MEDICINES THAT IMPROVE BLADDER DRAINING POWER |
| WO2002044159A2 (en) * | 2000-11-29 | 2002-06-06 | Eli Lilly And Company | 1-(2-m-methanesulfonamidophenylethyl)-4-(m-trifluoromethylphenyl)piperazine and pharmaceutically acceptable salts and solvates thereof and their use in the treatment of incontinence |
| WO2003000664A1 (de) * | 2001-06-22 | 2003-01-03 | Bayer Aktiengesellschaft | Uracilderivative und ihre verwendung bei der behandlung bakterieller erkrankungen |
| CN102657664A (zh) | 2003-09-12 | 2012-09-12 | 阿勒根公司 | 用于治疗疼痛和其它α2肾上腺素能介导疾病的方法及组合物 |
| US20050059744A1 (en) * | 2003-09-12 | 2005-03-17 | Allergan, Inc. | Methods and compositions for the treatment of pain and other alpha 2 adrenergic-mediated conditions |
| US20050058696A1 (en) * | 2003-09-12 | 2005-03-17 | Allergan, Inc. | Methods and compositions for the treatment of pain and other alpha 2 adrenergic-mediated conditions |
| US20060264442A1 (en) * | 2005-05-18 | 2006-11-23 | Allergan, Inc. | Methods for the treatment of ocular and neurodegenerative conditions in a mammal |
| CN101200451B (zh) * | 2006-12-15 | 2010-12-15 | 重庆药友制药有限责任公司 | 一种盐酸乌拉地尔的制备方法 |
| CN102295607B (zh) * | 2011-06-16 | 2013-04-17 | 郑州大学 | 乌拉地尔的逆相转移催化制备方法 |
| KR102638538B1 (ko) | 2021-12-28 | 2024-02-20 | 주식회사 한서켐 | 우라피딜 제조 중간체의 제조방법 |
| CN115477616A (zh) * | 2022-09-27 | 2022-12-16 | 河北广祥制药有限公司 | 一种乌拉地尔杂质的制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2567651A (en) * | 1951-09-11 | J-dialkyl-g-amino-l |
-
0
- BE BE755015D patent/BE755015A/xx not_active IP Right Cessation
-
1969
- 1969-08-20 DE DE1942405A patent/DE1942405C3/de not_active Expired
- 1969-12-19 BR BR215466/69A patent/BR6915466D0/pt unknown
-
1970
- 1970-07-30 CH CH346173A patent/CH582173A5/xx not_active IP Right Cessation
- 1970-07-30 CH CH1150970A patent/CH551990A/xx not_active IP Right Cessation
- 1970-08-13 SU SU1670154A patent/SU399130A3/ru active
- 1970-08-13 GB GB3908070A patent/GB1309324A/en not_active Expired
- 1970-08-14 YU YU02076/70A patent/YU36509B/xx unknown
- 1970-08-15 BG BG017052A patent/BG17796A3/xx unknown
- 1970-08-17 LU LU61527D patent/LU61527A1/xx unknown
- 1970-08-18 IL IL35121A patent/IL35121A/xx unknown
- 1970-08-19 BG BG017051A patent/BG17795A3/xx unknown
- 1970-08-19 FI FI2271/70A patent/FI54479C/fi active
- 1970-08-19 ES ES382842A patent/ES382842A1/es not_active Expired
- 1970-08-19 AT AT751370A patent/AT302359B/de not_active IP Right Cessation
- 1970-08-19 BG BG015509A patent/BG17585A3/xx unknown
- 1970-08-19 DK DK424770AA patent/DK124031B/da not_active IP Right Cessation
- 1970-08-19 AT AT959571A patent/AT318651B/de not_active IP Right Cessation
- 1970-08-19 SE SE7011321A patent/SE386448B/xx unknown
- 1970-08-19 NO NO03159/70A patent/NO129148B/no unknown
- 1970-08-19 HU HUBI373A patent/HU163664B/hu unknown
- 1970-08-20 NL NL707012364A patent/NL155014B/xx not_active IP Right Cessation
- 1970-08-20 FR FR7030598A patent/FR2073300B1/fr not_active Expired
- 1970-08-20 IE IE1084/70A patent/IE35177B1/xx unknown
- 1970-08-20 CA CA091,177A patent/CA956944A/en not_active Expired
- 1970-08-20 US US05/065,445 patent/US3957786A/en not_active Expired - Lifetime
- 1970-08-20 ZA ZA705729A patent/ZA705729B/xx unknown
-
1976
- 1976-04-08 US US05/675,122 patent/US4067982A/en not_active Expired - Lifetime
-
1978
- 1978-05-04 HK HK236/78A patent/HK23678A/xx unknown
-
1979
- 1979-08-20 YU YU02039/79A patent/YU36518B/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116082250A (zh) * | 2021-11-05 | 2023-05-09 | 江苏润安制药有限公司 | 一种新的制备盐酸乌拉地尔的方法 |
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PS | Patent sealed [section 19, patents act 1949] | ||
| PE20 | Patent expired after termination of 20 years |